Crystal structure and Hirshfeld surface analysis of a new polymorph of (E)-2-(4-bromo-phen-yl)-1-[2,2-di-bromo-1-(3-nitro-phen-yl)ethen-yl]diazene

Zeliha Atioğlu; Mehmet Akkurt; Namiq Q Shikhaliyev; Naila A Mammadova; Gülnara V Babayeva; Victor N Khrustalev; Ajaya Bhattarai

doi:10.1107/S2056989022007113

Crystal structure and Hirshfeld surface analysis of a new polymorph of (E)-2-(4-bromo-phen-yl)-1-[2,2-di-bromo-1-(3-nitro-phen-yl)ethen-yl]diazene

Acta Crystallogr E Crystallogr Commun. 2022 Jul 14;78(Pt 8):804-808. doi: 10.1107/S2056989022007113. eCollection 2022 Aug 1.

Authors

Zeliha Atioğlu¹, Mehmet Akkurt², Namiq Q Shikhaliyev³, Naila A Mammadova³, Gülnara V Babayeva^{3

4}, Victor N Khrustalev⁵, Ajaya Bhattarai⁶

Affiliations

¹ Department of Aircraft Electrics and Electronics, School of Applied Sciences, Cappadocia University, Mustafapaşa, 50420 Ürgüp, Nevşehir, Turkey.
² Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey.
³ Organic Chemistry Department, Baku State University, Z. Khalilov str. 23, AZ 1148 Baku, Azerbaijan.
⁴ Azerbaijan State Pedagogical University, Uzeyir Hajibeyli str., 68, Baku, Azerbaijan.
⁵ Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklay St. 6, Moscow, 117198, Russian Federation, N. D. Zelinsky Institute of Organic Chemistry RAS, Leninsky Prosp. 47, Moscow, 119991, Russian Federation.
⁶ Department of Chemistry, M.M.A.M.C (Tribhuvan University) Biratnagar, Nepal.

Abstract

A new polymorph of the title compound, C₁₄H₈Br₃N₃O₂, (form-2) was obtained in the same manner as the previously reported form-1 [Akkurt et al. (2022 ▸). Acta Cryst. E78, 732-736]. The structure of the new polymorph is stabilized by a C-H⋯O hydrogen bond that links mol-ecules into chains. These chains are linked by face-to-face π-π stacking inter-actions, resulting in a layered structure. Short inter-mol-ecular Br⋯O contacts and van der Waals inter-actions between the layers aid in the cohesion of the crystal packing. In the previously reported form-1, C-H⋯Br inter-actions connect mol-ecules into zigzag chains, which are linked by C-Br⋯π inter-actions into layers, whereas the van der Waals inter-actions between the layers stabilize the crystal packing of form-2. Hirshfeld mol-ecular surface analysis was used to compare the inter-molecular inter-actions of the polymorphs.

Keywords: C—H⋯O interactions; Hirshfeld surface analysis; azo compounds; crystal structure; polymorphism.

Grants and funding

This work was performed under the support of the Science Development Foundation under the President of the Republic of Azerbaijan (grant No. EIF-BGM-4- RFTF-1/2017–21/13/4).